The definition of a good sailor and a bad sailor are quite clear to practically anyone. A good sailor can sail fast even if the wind is not strong. A bad sailor gets stuck trying to maneuver in heavy winds. A good sailor is strong, bold, and able to succeed in any situation thrown at them. A bad sailor is the opposite.

Or so it is told to us as we grow up learning to sail. But recently I’ve realized that distinguishing between a good and bad sailor is a whole lot more difficult and complex than we are made to believe.

On the first Tuesday in the second session, a group of IITs took five or six 420s out to race. I was in a 420 with another IIT, Eddie. I was skippering and Eddie was crewing at this point. We sailed into the nook between the inner Boston Harbor and the Mystic River and set up our pins and committee boat to create a port triangle race course. The wind was a little fickle, rather calm; sometimes there was no wind, other times there was an intense amount.

In the first race, Eddie and I won; quite surprised as we did not think nor focus on winning. In the second race, we ended up getting stuck around the pin and sailing backwards; not even finishing before the committee boat started blowing the whistle for the third race’s start sequence.

Then Eddie took the tiller and we won again. But our plans soon backfired, again not finishing the fourth race, as we ended up sailing too far away from the line to be able to cross it. We sat out the next race trying to raise our main sail up the few annoying, ridiculously tough inches left on the mast. We succeeded a little bit, causing our sail to rise up maybe an inch, maybe not even that far. We decided to let it go and join in on the next race-this time doing well.

A few more races went by with Eddie and me switching every two races from the roomy skipper spot to the tiny crew space, where a 6’2” guy can’t fit his legs or head. We continued to do pretty well, plateauing in the top of the middle of the pack.

Eventually it was time to go in, and after a few occasions of the both of us freaking out over the main sail’s top baton back winding or the 420 heeling too much for our liking, Eddie and I were content with our morning sail, but tired enough to gladly go in and enjoy our lunch.

After the day was over, I continued to think about the 420 races. I thought about how many times Eddie had me laughing and how many times we both freaked out, either silently or out loud. I felt pride thinking about our continuous good starts and our few wins. I felt amused thinking about the two times we did not even finish a race. But most prominently, I thought about all of the times you could have defined Eddie and I as good sailors and then all of the times as bad sailors.

How can the two of us start a race right at the line, but, at the same time, struggle to figure out how to start moving again? How could we win a race and then the next race not even finish and then repeat that sequence again? How do we avoid being protested time after time but still manage to completely miss or run over the mark?

Because we are just sailors. We have those moments when everyone is amazed at what we just did. But we also have those moments when all we can do is shake our heads and chuckle. I believe we are good sailors—though not the way I originally thought a good sailor was. We are good sailors because we make mistakes. Because we completely miss the start line, finish line, or mark. Because we sail backwards without meaning to. Because we heel too much and freak out before remembering to hike out and ease the main sail. Because, most importantly, we come away from those mistakes as better sailors and with a good joke to tell everyone when we get back to the dock.

You can call anyone a good or bad sailor. It just depends on when you look at them while they sail. You can find me sailing smoothly and swiftly winning, but then the next person to see me can look at me without wind and very quickly drifting towards the Coast Guard base.

I now see that a good sailor does not get discouraged, is determined, smart, and courageous. It does not matter if you know or understand sail theory or not. It does not matter if you cannot master anchoring or docking. It only matters that you try and try and try until you can eventually succeed at the task. It does not matter if you won every race or did not finish every race. It only matters that you take that experience and feel pride, saying to yourself, “I went out there and was courageous”. Because, after all, that is why we are named Courageous Sailing.

Apparently there was some sailboat racing on Monday night--this thing we do every year called the Courageous Corporate Challenge. Yes, I was there. Yes, I watched said sailboat racing. You’re curious: “Who raced? Was it competitive? What were the conditions? Who won?” All questions will be answered....maybe.